Issue 4, 1993

Diastereo- and enantio-selectivity in the Pictet–Spengler reaction

Abstract

The factors that control the relative and absolute stereochemistry of 1,3-disubstituted and 1,2,3-trisubstituted tetrahydro-β-carbolines formed via the Pictet–Spengler reaction are discussed. In particular, the stereochemical factors that lead to the predominance of cis-1,3-disubstituted products under conditions of kinetic control are presented, with the aid of X-ray crystallographic data on a number of compounds; methods for assigning relative stereochemistry on the basis of NMR data are given; the mechanism by which racemisation can occur during the Pictet–Spengler reaction has also been studied, and procedures for eliminating this problem are given.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 431-439

Diastereo- and enantio-selectivity in the Pictet–Spengler reaction

P. D. Bailey, S. P. Hollinshead, N. R. McLay, K. Morgan, S. J. Palmer, S. N. Prince, C. D. Reynolds and S. D. Wood, J. Chem. Soc., Perkin Trans. 1, 1993, 431 DOI: 10.1039/P19930000431

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